US2279512A - Molding compound - Google Patents
Molding compound Download PDFInfo
- Publication number
- US2279512A US2279512A US349300A US34930040A US2279512A US 2279512 A US2279512 A US 2279512A US 349300 A US349300 A US 349300A US 34930040 A US34930040 A US 34930040A US 2279512 A US2279512 A US 2279512A
- Authority
- US
- United States
- Prior art keywords
- dicyandiamide
- phenol
- mole
- resin
- aldehyde
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
Definitions
- the invention includes the improved molding resins them selves, their methods of preparation, and the molded products obtained therefrom.
- the molding compound contains no curing material other than the alk ali its ageing properties are excellent and it can be stored for many months without impairing its molding properties.
- thermosetting resins from any of the grades of phenol describ in our earlier application identified above.
- heat treated mixtures of 'dicyandiamide with synthetic phenol, 395 phenol, 82% phenol we have found that heat treated mixtures of 'dicyandiamide with synthetic phenol, 395 phenol, 82% phenol,
- Ourpresent invention relates more particu-.
- This material consists of 82% CsHsOH, 8-14% meta and para-cresols and 4-10% o-cresol.
- a representative sample of-this material contains 0.25% o-cresol, 2.25% phenol, 73.5% of a mixture containing 60% meta and 40% para-cresol, 10.5% of a fractionconsisting of 20% meta. and para-cresols,
- the time of heating influences the properties.
- the amounts of dicyandiamide to be heated with the phenol may vary between rather wide limits, depending on the characteristics desired in the finished product. Ordinarily equimolecular ratios of phenol and-dicyandiamide are used, but where better heat resistance is desired it may be advisable to employ 2 or 3 moles of dicyandiamide for each mole of phenol.
- the product is condensed with formal- Q dehyde, acetaldehyde, benzaldehyde or other suitable aldehyde.
- the amount of aldehyde may vary from 2.7 to 5 moles for each mole of the phenol-dicyandiamidei mixture.
- thi ldehyde should first be mixed with 'sufilcient a ounts of an alkali having bufiering' propertiesto raise the pH to about 9.1-9.5 and preferably to about 9.3.
- Sodium and potassium carbonate are the best compounds that we have found for this purpose, but sodium silicate, sodium borate, and trisodium phosphate or their potassium equivalents may also be used.
- These or similar compounds may be added to the aldehyde as the dry solid or in solutions, using amounts sufli'cient to raise the pH to the desired figure.
- the condensation of the aldehyde containing these butters with the heat-treated material is then carried out by heating the charge to refluxing temperatures which are about 96-98 C., and refluxing for about hour or longer, depending on the purpose for which the resin is to be used. It will be noted that this is a much shorter time than is recommended for molding compounds when caustic soda is used as the alkali.
- the charge After refluxing the charge for the desired period of time it is dehydrated. This step is preferably carried out by applying a vacuum to the kettle such that most of the water can be removed at 72-76 C. Near the end point of the dehydration the temperature will riseto about 95-110 C., depending on the type of resin and 5 time of reflux, and the charge is poured at this temperature after the last of the water has been evolved. It. cools to a hard,.brittle mass which will be clear if nitrogen was used as the inert gas in the kettle but slightly cloudy if carbon dioxide was used.
- the resin is preferably finely ground (150-300 mesh). It is then thoroughly blended with a lubricant such as a mixture of calcium and zinc stearates, zinc l5 oleate or the like.
- a filler such as wood flour. alpha-pulp, asbestos, diatomaceous earth, mica or similar material and a suitable amount of other at 135 C., for 1.5 minutes when using awood flour filler and 1 to 3 minutes with alphapulp -filler and the resulting sheets are then ground to a particle size suitable for molding which may be done with or without a preliminary pelleting.
- the resin syrup may b'epoured directly onto a blended mixture of the filler, lubricant and dye in a Banbury mixer at temperatures oi" 60-90". C. and mixed until the filler is thoroughly coated.
- the mass may then be dried-with or without vacuum under controlled conditions until substantially all the water is'removed after which it may be ground if desired.
- Example 1 Equimolecular quantities of dicyandiamide and 39.5,phenol are 'heated and refluxed at atmospheric pressure for 4 hours. Shortly after the. heating is begun an evolution of ammonia is noted and the refluxing is continued until about i 0.10 to 0.18'mole, and preferably about 0.15 mole,
- the pH of the mixture was 9.3, and the same value was also found when the condensation was com-- pleted.
- the condensation product was then dehydratedby heating under. a 21 inch' vacuum and the resin was cooled and ground to -300 mesh.
- a molding compound was prepared by. intimately mixing 400 parts of the ground resin, 216 parts of alpha pulp and 3 parts of calcium stearate or other suitable lubricant. The mixture 0 about 30 minutes. At the beginning of the reflux color.
- portions of the batch were molded into tumblers, using a steam-heated press at 150-160 C.
- Example 2 23.6 parts by weight of dicyandiamide and 26.4 parts of 82% phenol arev heated and refluxed at atmospheric pressure with continuous agitation for 4 hours. Shortly after the heating is begun an evolution of ammonia is noted, and
- a molding compound is prepared by intimately mixing 400 parts of the resin, 400 parts of wood flour and 4' parts of calcium stearate with suitable amount of dyestufl to give the required The mixture is blended thoroughly and then compounded on steam-heated differential rolls at 100-110 C. for 0.75 to 2.5 minutes, depending on the flow desired. The material may then be ground leted if desired.
- Example 3 or other filler together with a lubricant.
- the resulting molding compound is well suited for a largevariety of purposes, since it can be molded to pieces which are fairly light in color 'and possess good dielectric strength, excellent arc resistance and retain their dimensions under the most extreme conditions of humidity.
- Example 4 parts of Barrett Cresylic Acid (212 0.) and 18.5 parts of dicyandiamide are heat-treated to suitable particle size and pel-- This solution is then .flour, or suitable amounts of diatomaceous earth.
- resin is dehydrated under a vacuum, cooled and ground to -300'mesh or finer.
- the ground resinare 400 parts of the ground resinare mixedwith-an equal weight of wood flour or suitable amounts of other fillers such as mica, diatomaceous earth, cotton flock, etc., together with a lubricant such as calcium stearate.
- thermos'ettingresin capable of being cured without further addition of catalyst which comprises condensing with an aldehyde the material obtained upon heating dicyandiamide and a phenol until from.0.07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while'maintaining the and 9.5 throughout the aldehyde condensation.
- thermosetting resin capable of being cured without further addition of catalyst which comprises condensing with an upon heating dicyandiamide and a phenolic mixture containing an alkyl phenol untilfrom .07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while maintaining the pH at a relatively constant value between about 9.1 and 9.5 throughout the aldehyde condensation.
- thermosetting resin capable of being cured without further ad dition of-catalyst which comprises condensi'ngr I
- thermosetting resin capable of being cured without further addition oi catalyst which comprises condensing with an aldehyde the material obtained upon heating dicyandiamide and 82% phenol until from 0.13 to 0.18 mole of ammonia per mole of' dicyandiamide are evolved while maintainingthe pH at a, relatively constant value between about 9.1 and 9.5 throughout-the aldehyde condensation.
- a synthetic resin of the thermosetting type capable of being cured'without further addition of catalyst. said resin being the condensation product. of an aldehyde with the material obpH at a relatively constant value between about 9.1
- a synthetic resin of thethermosetting type capable of being cured without further addition of catalyst, said resin being the condensation product of an aldehyde with the material obtained upon heating a mixture of dicyandiamide and 82% phenol until from .07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while maintaining the pH at a relatively constant value between about 9.1 and 9.5 throughout the aldehyde condensation.
- a molding composition comprising a filler and a synthetic resin of the thermosetting type capable of being cured without further addition of catalyst, said resin being the condensation product of an aldehyde with the material obtained upon heating a mixture of dicyandiamide and a phenol until from .07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while maintaining the pH at a relatively constant value between about 9.1 and 9.5 throughout the aldehyde condensation.
- a molding composition comprising a filler and a synthetic resin of the thermosetting type capable of being cured without further addition of catalyst, said resin being the condensation product of an aldehyde with the material obtained upon heating a mixture of dicyandiamide and a phenolic mixture containing an alkyl phenol until from .07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while maintaining the pH at a relatively constant value between about 9.1 and 9.5 throughout the aldehyde condensation.
- a molding composition comprising a filler and a synthetic resin of the thermosetting type capable of being cured without further addition of catalyst, said resin being the condensation product ofan aldehyde with the material obtained upon heating a mixture of dicyandiamide and a cresol until from .07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while maintaining the pH at a relatively constant value between about 9.1 and 9.5 throughout the aldehyde condensation.
- a molding composition comprising a filler and a synthetic resin of the thermosetting type capable of being cured without further addition of catalyst, said resin being the condensation product of an aldehyde with the material obtained upon heating a mixture of dicyandiamide and 82% phenol until from .07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while maintaining the pH at a. relatively constant value between about 9.1 and 9.5 throughout the aldehyde condensation.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
Patented Apr. 14, 1942 Frank J. Grotenand James B.
Lower, Stamford,
Conn., assignors to American Cyanamid Company, New York, Y., a corporation of Maine No Drawing. Application August 1, 1940,
Serial No. 349,300 12 Claims. 280-45) This invention-relates to an improvement iu.
' the new class of resinous molding compounds 'described'in ourc'opending application Serial No.
256,772, filed February 16, 1939, now .Patent No. 2,229,291, dated January 21, 1941. The invention includes the improved molding resins them selves, their methods of preparation, and the molded products obtained therefrom.
In theabove identified application we have described a class of molding compounds prepared from a new type of synthetic resin which 'isan aldehyde condensation product of the material obtained upon heating dicyandiamide with a phenol until substantial quantities of'. ammonia are given off and most of the dicyandiamide is converted into .cyclic compounds. The molded products described in that applicaheat and pressure, without the addition of any objects having an even better surface appearance than those obtainable by using an acid catalyst, as described in our prior application. Moreover,
othercatalyst or curing agent whatsoever, into the moldability of our new resins extends over tion :are prepared by .mixing these heat-treated dicyandiamide-phenol resins with small quantities of an acidic curing agent, together with lubricants and fillers, and molding the resulting" compound under heat and pressure for suitable periods of time.
a much wider range than is possessed by our earlier compounds, which means that eithera rapid cure or a slower cure with better flow properties in the mold can be obtained at will. Since the molding compound contains no curing material other than the alk ali its ageing properties are excellent and it can be stored for many months without impairing its molding properties.
We have found that the principles of .our invention are equally applicable to the preparation of thermosetting resins from any of the grades of phenol describ in our earlier application identified above. In'o'ther words, we have found that heat treated mixtures of 'dicyandiamide with synthetic phenol, 395 phenol, 82% phenol,
- and lower grades of phenols containing cresols,
Ourpresent invention relates more particu-.
' larly to an improvement in the steps of condensing the heat-treated dicyandiamide-phenol mixture with formaldehyde or other'aldehyde and the subsequent preparation of molding compounds. In our prior application. we pointed out that the formaldehyde should preferably be ad- H. of 9.1-9.5 'before condensing it iusted to a with the eat-treated dicyandiamide-phenol mixture, in order to avoidgelation of the resin, but we stated that during the aldehyde condensation reaction a drop in the pH' to 7.2-7.6 would benoted.
Further investigations .have shown that this drop in pH during the formaldehyde condensation was due to the fact that we employed sodium hydroxide ,for neutralizing the formaldehyde.
or no bufiering action-and also causes the.de-
.This material, like other free alkalies, has little composition of formaldehyde to formic acid' and methanol, which isthe well-known Cannizzaro reaction. The formic acid produced by this reaction caused the-rapid drop in pH that was noted during the formaldehydecondensation.
By replacing the sodium hydroxide with other alkalies having a buifering-action we have suc- I ceeded in maintaining the pH at a constant value between about 9.1 and 9.5 throughout the formaldehyde condensatiomand we have obtained a new type of' resin having entirely different and r unexpected properties. This resin can be mixed with fillers and lubricants and molded under xylenols and the like, can be condensed with formaldehyde,'acetaldehyde, benzaldehyde, fur-.
fural and .other reactive aldehydesat a pH of about 9.1 to 9.5 to form resins, all of which are capable of beingcuredat ordina'ry molding temperatures of ISO-175 F. or higher without the addition of catalysts or curing agents. The following is .a description of the phenols which we have used in preparing our new resins:
(1') Synthetic phenol. This is the C. Pimaterial and consists of practically 100% CsHsQH.
(2) 395 phenol. This is the highest grade of coal 'tar phenol obtainable. It contains .between 99 and 99.5% CsHsOH.
(3) 82% phenol. This material consists of 82% CsHsOH, 8-14% meta and para-cresols and 4-10% o-cresol.
(4) Barrett No. 8 Cresol." A representative sample of-this material contains 0.25% o-cresol, 2.25% phenol, 73.5% of a mixture containing 60% meta and 40% para-cresol, 10.5% of a fractionconsisting of 20% meta. and para-cresols,
60% 1.2.4 xylenol and 20% 1.3.5 xylenol and known as the :r1, fraction, and 13.5% of a fraction boiling between 204 C, and 210 .0.
Half of this fraction is meta and para-cresols and the other halfis the\:c-1- fraction having the composition indicated above.
(5) fBarrett Cresylic Acid (212 C.) A top-- resentative sample of this material contains 10.8% phenol, 1.2% o-cresol, 20% meta ancl para-cresols, 20%"a:-1-" fraction, 20% 1.2.4
in a jacketed kettle provided with an agitator and dicyandiamide is added. The charge is heated with stirring to the reflux temperature of the phenol, which is about 181-212 C. and
maintained at these temperatures with agitation for about 2.5-5.5 hours. During this timeammonia is given off and is allowed to escape. The time of heating can be shortened to 1.5 hours if an acid condensing agent such as anhydrous zinc chloride is added in amounts of 0.5% of the weight of the dicyandiamide, as described in the copending application of J. T. Thurston et al, Serial No. 301,766, filed October 28, 1939.
The time of heating influences the properties.
of the finished product. -We have found that upon continued heating as much as 0.2 mole of ammonia can be driven off for each mole of dicyandiamide charged, but in most cases a shorter heating period and correspondingly reduced ammonia evolution is recommended. Ordinarily the best results are obtained when from 0.13 to 0.18 mole of ammonia per mole of dicyandiamide are liberated, but we have obtained resins of good properties with much shorter heating periods and i with the evolution of as little as 0.07-0.10 mole of ammonia per mole of dicyandiamide. It is sometimes desirable to carry out the refluxing in an atmosphere of an inert gas such as nitrogen or carbon dioxide in order to exclude oxygen. I
The amounts of dicyandiamide to be heated with the phenol may vary between rather wide limits, depending on the characteristics desired in the finished product. Ordinarily equimolecular ratios of phenol and-dicyandiamide are used, but where better heat resistance is desired it may be advisable to employ 2 or 3 moles of dicyandiamide for each mole of phenol.
After cooling the heattreated material tobelow 100 C. the product is condensed with formal- Q dehyde, acetaldehyde, benzaldehyde or other suitable aldehyde. The amount of aldehyde may vary from 2.7 to 5 moles for each mole of the phenol-dicyandiamidei mixture. As has been stated, thi ldehyde should first be mixed with 'sufilcient a ounts of an alkali having bufiering' propertiesto raise the pH to about 9.1-9.5 and preferably to about 9.3. Sodium and potassium carbonate are the best compounds that we have found for this purpose, but sodium silicate, sodium borate, and trisodium phosphate or their potassium equivalents may also be used. These or similar compounds may be added to the aldehyde as the dry solid or in solutions, using amounts sufli'cient to raise the pH to the desired figure. The condensation of the aldehyde containing these butters with the heat-treated material is then carried out by heating the charge to refluxing temperatures which are about 96-98 C., and refluxing for about hour or longer, depending on the purpose for which the resin is to be used. It will be noted that this is a much shorter time than is recommended for molding compounds when caustic soda is used as the alkali.
After refluxing the charge for the desired period of time it is dehydrated. This step is preferably carried out by applying a vacuum to the kettle such that most of the water can be removed at 72-76 C. Near the end point of the dehydration the temperature will riseto about 95-110 C., depending on the type of resin and 5 time of reflux, and the charge is poured at this temperature after the last of the water has been evolved. It. cools to a hard,.brittle mass which will be clear if nitrogen was used as the inert gas in the kettle but slightly cloudy if carbon dioxide was used.
To prepare the molding compound, the resin is preferably finely ground (150-300 mesh). It is then thoroughly blended with a lubricant such as a mixture of calcium and zinc stearates, zinc l5 oleate or the like. A filler such as wood flour. alpha-pulp, asbestos, diatomaceous earth, mica or similar material and a suitable amount of other at 135 C., for 1.5 minutes when using awood flour filler and 1 to 3 minutes with alphapulp -filler and the resulting sheets are then ground to a particle size suitable for molding which may be done with or without a preliminary pelleting.
An alternative process which may be employed -'in the preparation of impregnated sheets or in preparing molding compounds is to omit the vacuum dehydration leaving the resin in syrup form. This syrup may be soaked into absorbent paper sheets which are then dried and pressed out in a flat mold to make a laminated board.
Similarly, the resin syrup may b'epoured directly onto a blended mixture of the filler, lubricant and dye in a Banbury mixer at temperatures oi" 60-90". C. and mixed until the filler is thoroughly coated. The mass may then be dried-with or without vacuum under controlled conditions until substantially all the water is'removed after which it may be ground if desired.
The invention will be illustrated in greater de tail by the following specific examples. It should be understood, however, that these examples are given primarily for purposes of illustration, and, that the invention in its broader aspects is not limited thereto.
Example 1 Equimolecular quantities of dicyandiamide and 39.5,phenol are 'heated and refluxed at atmospheric pressure for 4 hours. Shortly after the. heating is begun an evolution of ammonia is noted and the refluxing is continued until about i 0.10 to 0.18'mole, and preferably about 0.15 mole,
' of ammonia have been givenofi for each mole of dicyandiamide charged. The mixture 'is then cooled to below 100? C.
1.85 lbs. of anhydrous sodium carbonate were added to 119.2 lbs. of 37 aqueous formaldehyde solution, which was then mixed with lbs.
of the cooled reaction mixture described above.
The formaldehyde condensation was then carried out by refluxing the mixture at 96-98 C. for
the pH of the mixture was 9.3, and the same value was also found when the condensation was com-- pleted. The condensation product was then dehydratedby heating under. a 21 inch' vacuum and the resin was cooled and ground to -300 mesh.
.A molding compound was prepared by. intimately mixing 400 parts of the ground resin, 216 parts of alpha pulp and 3 parts of calcium stearate or other suitable lubricant. The mixture 0 about 30 minutes. At the beginning of the reflux color.
was blended thoroughly and then compounded onsteam-heated diflerential rolls at 100 and 135 C. for 0.75 to 2.5 minutes, depending on the flow desired. After grinding to suitable particle size,
portions of the batch were molded into tumblers, using a steam-heated press at 150-160 C. The
, pieces were found -to have a light cream color, ex-
150 cc. of water for 30 minutes to. extract any free phenol that might be present. The water was then drained ofl.,-cooled to room temperature, and bromine water was added drop by drop to a cc. sample until it was saturated as indicated by a yellow color. No precipitate was formed, indicating a complete absence of free phenol in the molded resin as this test is very sensitive.
Example 2 23.6 parts by weight of dicyandiamide and 26.4 parts of 82% phenol arev heated and refluxed at atmospheric pressure with continuous agitation for 4 hours. Shortly after the heating is begun an evolution of ammonia is noted, and
the refluxing is continued until about 0.15 mole of ammonia have been of dicyandiamide charged. The mixture isthen cooled to below 100 C. I
60.8 parts of 37.5% formaldehyde solution given off for each mole are neutralized by the addition of sodium carbonate to a pH of 9.1. added to the cooled reaction mixture and the formaldehyde condensationis carried out with refluxing at 96--98 C. for about hour. The condensation product is dehydrated by heating under a 21 inch vacuum until all the water is removed and the resin, upon cooling, is hard and brittle. The resin is then cooled to room temperatures and ground to 150-300 mesh.
A molding compound is prepared by intimately mixing 400 parts of the resin, 400 parts of wood flour and 4' parts of calcium stearate with suitable amount of dyestufl to give the required The mixture is blended thoroughly and then compounded on steam-heated differential rolls at 100-110 C. for 0.75 to 2.5 minutes, depending on the flow desired. The material may then be ground leted if desired.
. Example 3 or other filler together with a lubricant. The resulting molding compound is well suited for a largevariety of purposes, since it can be molded to pieces which are fairly light in color 'and possess good dielectric strength, excellent arc resistance and retain their dimensions under the most extreme conditions of humidity.
Example 4 27, parts of Barrett Cresylic Acid (212 0.) and 18.5 parts of dicyandiamide are heat-treated to suitable particle size and pel-- This solution is then .flour, or suitable amounts of diatomaceous earth.
as in Example 1 until about 0.13 mole of am- 1 monia areevolved for each mole oi dicyandialdehyde the material obtained 3 amide. The product is condensed with" 46 parts of 37.5%iormaldehyde solution neutralized with borax to a pH of 9.4 after which the resulting.
resin is dehydrated under a vacuum, cooled and ground to -300'mesh or finer.
400 parts of the ground resinare mixedwith-an equal weight of wood flour or suitable amounts of other fillers such as mica, diatomaceous earth, cotton flock, etc., together with a lubricant such as calcium stearate. The resulting powder-can be cured in 1 minute under ordinary molding conditions and is therefore a good general purpose molding compound for producing any. type of molded article in which the lightest color is not required. It is particularly valuable for its good electrical properties and moisture resistance.
This is a continuation-in-part of our copending application, Serial No. 256,772. filed February 16, 1939. now Patent No.,2,229,291, dated January- 21, 1941. o
We claimz l. A method of preparing a thermos'ettingresin capable of being cured without further addition of catalyst which comprises condensing with an aldehyde the material obtained upon heating dicyandiamide and a phenol until from.0.07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while'maintaining the and 9.5 throughout the aldehyde condensation.
2. A method of preparing a thermosetting resin capable of being cured without further addition of catalyst which comprises condensing with an upon heating dicyandiamide and a phenolic mixture containing an alkyl phenol untilfrom .07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while maintaining the pH at a relatively constant value between about 9.1 and 9.5 throughout the aldehyde condensation.
3. A method oi preparing a thermosetting resin capable of being cured without further ad dition of-catalyst which comprises condensi'ngr I,
with Ian aldehyde the material obtained upon heating dicyandiamide and a cresol until from .07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while maintaining the pI-li at a relatively constant value between about 91.1 and 9.5 throughout the aldehyde condensat on.
4. A method of preparing a thermosetting resin capable of being cured without further addition oi catalyst which comprises condensing with an aldehyde the material obtained upon heating dicyandiamide and 82% phenol until from 0.13 to 0.18 mole of ammonia per mole of' dicyandiamide are evolved while maintainingthe pH at a, relatively constant value between about 9.1 and 9.5 throughout-the aldehyde condensation.
5. A synthetic resin of the thermosetting type capable of being cured'without further addition of catalyst. said resin being the condensation product. of an aldehyde with the material obpH at a relatively constant value between about 9.1
from .07 to 0.18 mole oi ammonia per mole of dicyandiamide are evolved while maintaining the pH at a relatively constant value between about 9.1 and .95 throughout the aldehyde condensation.
'7. A Synthetic resin of the thermosetting type capable of being cured without further addition of catalyst, said resin being the condensation product of an aldehyde with the material obtained upon heating a mixture of dicyandiamide and a cresol until from .07 to 0.18 mole of am- 'monia permole of dicyandiamide are evolved while maintaining the pH at a relatively constant value-between about 9.1 and 9.5 throughout the aldehyde condensation.
8. A synthetic resin of thethermosetting type capable of being cured without further addition of catalyst, said resin being the condensation product of an aldehyde with the material obtained upon heating a mixture of dicyandiamide and 82% phenol until from .07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while maintaining the pH at a relatively constant value between about 9.1 and 9.5 throughout the aldehyde condensation.
'9. A molding composition comprising a filler and a synthetic resin of the thermosetting type capable of being cured without further addition of catalyst, said resin being the condensation product of an aldehyde with the material obtained upon heating a mixture of dicyandiamide and a phenol until from .07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while maintaining the pH at a relatively constant value between about 9.1 and 9.5 throughout the aldehyde condensation.
10. A molding composition comprising a filler and a synthetic resin of the thermosetting type capable of being cured without further addition of catalyst, said resin being the condensation product of an aldehyde with the material obtained upon heating a mixture of dicyandiamide and a phenolic mixture containing an alkyl phenol until from .07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while maintaining the pH at a relatively constant value between about 9.1 and 9.5 throughout the aldehyde condensation.
11. A molding composition comprising a filler and a synthetic resin of the thermosetting type capable of being cured without further addition of catalyst, said resin being the condensation product ofan aldehyde with the material obtained upon heating a mixture of dicyandiamide and a cresol until from .07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while maintaining the pH at a relatively constant value between about 9.1 and 9.5 throughout the aldehyde condensation.
12. A molding composition comprising a filler and a synthetic resin of the thermosetting type capable of being cured without further addition of catalyst, said resin being the condensation product of an aldehyde with the material obtained upon heating a mixture of dicyandiamide and 82% phenol until from .07 to 0.18 mole of ammonia per mole of dicyandiamide are evolved while maintaining the pH at a. relatively constant value between about 9.1 and 9.5 throughout the aldehyde condensation.
FRANK J. GROTEN. JAMES H. LOWER.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US349300A US2279512A (en) | 1940-08-01 | 1940-08-01 | Molding compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US349300A US2279512A (en) | 1940-08-01 | 1940-08-01 | Molding compound |
Publications (1)
Publication Number | Publication Date |
---|---|
US2279512A true US2279512A (en) | 1942-04-14 |
Family
ID=23371774
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US349300A Expired - Lifetime US2279512A (en) | 1940-08-01 | 1940-08-01 | Molding compound |
Country Status (1)
Country | Link |
---|---|
US (1) | US2279512A (en) |
-
1940
- 1940-08-01 US US349300A patent/US2279512A/en not_active Expired - Lifetime
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5300593A (en) | Lignin modified binding agents | |
US1955731A (en) | Phenol resin and process of making the same | |
US2441860A (en) | Accelerated curing of phenol-form-aldehyde resins to the infusible state with 3, 5-xyenol | |
US2385373A (en) | Method of producing a resin and product derived therefrom | |
US3425989A (en) | Phenol condensation process comprising reacting anhydrous phenol and an alkali catalyst at a temperature of at least 130 c.,and then slowly adding aldehyde | |
US4337334A (en) | Process for production of phenolic resin from bisphenol-A by-products | |
US3471443A (en) | Curing phenol-aldehyde novolak resins employing aniline or aniline hcl | |
US2279512A (en) | Molding compound | |
US2563614A (en) | Phenolic resin and method of making | |
US1717600A (en) | Phenol-resin composition | |
US3083183A (en) | Process for producing phenolic resins using zinc borates as condensing agents | |
US2715114A (en) | Phenolic resins | |
US3464956A (en) | Ammonium biborate and ammonium pentaborate catalyzed and co - reacted phenol formaldehyde resins | |
US4011280A (en) | Process for the production of binders for weather-proof wood materials and product | |
US2951058A (en) | Resinous curing process using tetrahydro-1 h-oxazolo-(3, 4, c)-oxazole-7 a-methanol | |
US3042655A (en) | Novolak and method of manufacture thereof | |
US1974605A (en) | Resinous composition from phenol and acetaldehyde and process of making same | |
US2163264A (en) | Condensation products from formaldehyde and urea | |
US1705494A (en) | Condensation product of phenols and polyhydric alcohols | |
US2221511A (en) | Resinous composition and method of making the same | |
US1917248A (en) | Phenol-furfural resin and method of making the same | |
US2215596A (en) | Process of preparing resinous compositions | |
US2312431A (en) | Oil-modified composition and its preparation | |
US1269627A (en) | Process of hardening phenolic condensation products. | |
US2576735A (en) | Nitrogenous resins from ketonealdehyde-nitrogenous base and phenol-aldehyde |